This proposal describes a novel approach to the synthesis of functional analogs of the naturally occurring mitomycins. The routes proposed employ an interesting synthetic design in which well-known photochemical and thermal reactions are used to construct the basic pyrroloindoloquinone backbone, present in the mitomycins, from readily preparable starting materials. The analogs chosen will contain functional groups which serve to mimic those in the natural material that are presumed to be responsible for its drug activity. The course of the proposed research will proceed through the following phases: 1. Preparation of various substituted 1,2- dihydropyridinyl-1,4-benzoquinones and analogous pyridonylquinones which will serve as starting materials for ensuing photochemical-thermal reaction sequences. 2. Development of methods for accomplishing conversion of the dihydropyridinyl- and pyridonylquinones to the pyrroloindoloquinone ring systems by photochemical-thermal reaction sequences. 3. Introduction and conversion of functional groups at important positions on the basic backbone in order to derive compounds with more suitable chemotherapeutic properties.